Wittmann, I; Schierling, A; Dettner, K; Göhl, M; Schmidt, J; Seifert, K: Detection of a new Piperideine Alkaloid in the Pygidial Glands of Some Stenus Beetles, Chemistry and Biodiversity, 12(9), 1422-1434 (2015)

Rove beetles of the genus Stenus produce and store bioactive alkaloids like stenusine (3), 3-(2-
methylbut-1-enyl)pyridine (4), and cicindeloine (5) in their pygidial glands to protect themselves from
predation and microorganismic infestation.
The biosynthesis of stenusine (3), 3-(2-methylbut-1-enyl)pyridine (4), and cicindeloine (5) was previously
investigated in Stenus bimaculatus, Stenus similis, and Stenus solutus, respectively. The piperideine
alkaloid cicindeloine (5) occurs also as a major compound in the pygidial gland secretion of Stenus
cicindeloides. The three metabolites follow the same biosynthetic pathway, where the N-heterocyclic ring
is derived from l-lysine and the side chain from l-isoleucine. The different alkaloids are finally obtained
by few modifications of shared precursor molecules, such as 2,3,4,5-tetrahydro-5-(2-methylbutylidene)-
pyridine (1). This piperideine alkaloid was synthesized and detected by GC/MS and GC at a chiral phase
in the pygidial glands of Stenus similis, Stenus tarsalis, and Stenus cicindeloides.

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